A mural on a building with a man holding a machine and a sign that says "THIS LAND IS YOUR LAND".

Historic Route 66 Kid friendly Vacations

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Top Kid friendly vacation packages in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
  • Dec 23 - Dec 28

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.4/10 - Very good (3,161 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - HND • 1 stop
    ¥332,628
    ¥301,823
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Dec 23 - Dec 28

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (5,645 reviews)
    "El mejor lugar para quedarte en Chicago⭐️"
    Reviewed November 4, 2026
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - HND • 1 stop
    ¥413,706
    ¥343,300
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Dec 23 - Dec 28

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (194 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - HND • 1 stop
    ¥343,984
    ¥311,279
    per traveler
    found 1 day ago
    The Talbott, Autograph Collection
  • Dec 23 - Dec 28

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - HND • 1 stop
    ¥363,885
    ¥330,474
    per traveler
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Dec 23 - Dec 28

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,886 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - HND • 1 stop
    ¥355,700
    ¥323,367
    per traveler
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

Top Kid friendly Historic Route 66 Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

FAQs: family vacation packages in Historic Route 66

How can I find the best family vacation packages in Historic Route 66?

For fam-tastic vacation packages in Historic Route 66, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Historic Route 66 on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Historic Route 66 cost?

You could book your amazing family trip to Historic Route 66 just ¥301,823. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive Historic Route 66 family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Historic Route 66?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Historic Route 66 family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Historic Route 66 landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Historic Route 66 family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Historic Route 66 family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.